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Howland often played eccentric and rural roles in Hollywood. His parts were often small and uncredited, and he never got a leading role. He was a personal favorite of [[David O. Selznick]],{{citation needed|date=March 2017}} who cast him in his movies ''[[Nothing Sacred (film)|Nothing Sacred]]'' (1937) as a strange luggage man, ''[[The Adventures of Tom Sawyer (1938 film)|The Adventures of Tom Sawyer]]'' (1938, as the teacher Mr. Dobbins) and ''[[Gone with the Wind (film)|Gone with the Wind]]'' (1939) as a carpetbagger businessman.<ref name="bio">{{cite web |url=https://www.nytimes.com/movies/person/33602/Olin-Howland |title=Olin Howland |accessdate=February 3, 2016 |work=NY Times}}</ref> He also played in numerous westerns from [[Republic Pictures]], including the [[John Wayne]] films ''[[In Old California (1942 film)|In Old California]]'' (1942) and ''[[Angel and the Badman]]'' (1947). As a young man, Howland learned to fly at the [[Wright Flying School]] and soloed on a [[Wright Model B]]. This lent special sentiment in his scenes with [[James Stewart]] in the film ''[[The Spirit of St. Louis (film)|The Spirit of St. Louis]]'' (1957), as Stewart was also a pilot in real life. ''The Spirit of St. Louis'' and ''[[The Blob|Them (1954)]]'',where he played a drunken old man, and The Blob (1958) were his last films.
He also played in television shows during the 1950's. One of Olin's memorable television appearances was in an episode of "I Love Lucy. " Entitled "First Stop", air date 17 January 1955 Olin played the humorous role of a cafe and motel owner offering dubious accommodations to the road-weary Ricardos and Mertzes as they traveled by car on their way to Hollywood. In 1958 and 1959, he was cast as Charley Perkins in five episodes of [[American Broadcasting Company|ABC]]'s [[sitcom]] ''[[The Real McCoys]]'', starring [[Walter Brennan]].
Howland never married and had no children. He worked until his death in [[Hollywood]], California, at the age of 73.
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